1987•Advances in chemistry seriesRequires access
Nucleophilic Reactivity in Gas-Phase Anion—Molecule Reactions
Richard N. McDonald, A. Kasem Chowdhury, Wei Yi Gung, Krisma Deylene. Dewitt
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Abstract
Three different topics of nucleophilic anions reacting with neutral molecules are discussed. (1) O 2 · - is established intrinsically and kinetically as a super nucleophile in S N 2 reactions with CH 3 X molecules. (2) The intrinsic reactivity scale of nucleophilic additions to carbonyl centers is developed by using C 6 H 5 N· - as the nucleophile and can be extended with (C 6 H 5 ) 2 C· - . (3) The phosphoryl anion (CH 3 O) 2 PO - is shown to be a poor nucleophile in S N 2 reactions with CH 3 X molecules but reacts rapidly with ICF 3 and BrCF 3 by initial electron transfer; mainly (CH 3 O)(X)P 2 - negative ions result.